It is September, well past Labor Day and the season is officially changing! The fashionably intelligent gentleman knows that trends come and go but there are always those classic pieces that ring most true for each season. Below, are five pieces that we believe should be more curated for the fall as opposed to simply being purchased. Just think before you purchase these items. For they are the backbone of any gentleman’s fall wardrobe and warrant the investment.

ONE: The Trench
This is sort of like a friend that you’ll always have around. He never lets you down, especially when those spring showers come around. But he also gives you a lot of mileage as the fall season begins and paves way for a winter filled with harsh elements. Best of all, he doesn’t cramp your style when you’re wearing a suit. As a tip, invest in a classic style like in tan or black. Subtle patterns are fine; just don’t make your only trench a bright red one.

TWO: The Chambray Shirt
This piece started as a trend but the heavily twilled cotton is here to stay. A staple in retailers like J.Crew and Gant, it is the perfect shirt for looking professional and also staying warm and stylish all at the same time. In blue, Chambray has never looked better. It is the perfect complement to browns, tobaccos, camel and virtually any other color you fancy.

THREE: The Tweed Jacket
Other than the obvious warming function of this piece, the tweed jacket brings unrivaled fashion flexibility to your outfits during the fall season. Channel upscale easily with a crisp shirt and trousers. Simultaneously, express casual cool with denim and even a t-shirt.

FOUR: Cashmere Cardigan
Yes it’s luxurious and elegant and no, it’s not only for women. Cashmere, especially in a staple like a cardigan, catapults the garment’s practicality to the realms of the plush. Indeed, this one is for the fashionably intelligent. A creative alternative to  blazer, it brings with it a sense that is untroubled, perfectly suitable for the office or an evening out on the town.

FIVE: Wingtips
Wingtips are the perfect piece of fall footwear. The low-heeled shoe is uniquely characterized by robust leather and decorative perforations. This brings forth a sense of functionalism and elegance. Much like the tweed jacket, wingtips double up as dressy and casual at the same time.

It is inevitable that when you are from New England and have an affinity for your boat shoes and Nantucket reds, (or a rope belt or anything with an anchor on it) you are going to be made fun of. The truth is, preppy style is a credible movement and a defined American style that has inspired the world over, even the Italians.

The trick is not don all the aforementioned items together at the same time.

Consider the following combinations for a look of great Prep style:

1. Boat shoes, khakis and a grey tee. The combination does not call too much attention to itself and stays in prepster territory sans the Wasp jokes, keeping your integrity intact.

2. If you’re going to wear anything with an unmistakable nautical theme make sure it’s the only nautical thing you’re wearing. For example, if you’re into those rope belts then pair that with flat front grey or tan shorts and a simple button down shirt.

Stripes

3. Stripes are considered heavily nautical, French and preppy too. Due to their classic propensity, we now seem them all year round. A sweater with wide horizontal navy stripes is a great look with chinos and a trench.

4. Whimsy is fun. Anchor prints on a tie or a shirt or even whales repeating on trousers or shorts are fun. Just pair with solids and don’t overdo the bright colors. Stick to one fun element and keep everything else restrained. It will make you more interesting and actually highlight some whimsy but in an understated way.

Although it may not be present in all its glory, Spring is here. Dress up for the weekend and for the jaunty season.  For a comfortable and relaxed look, incorporate bright colors, with breathable fabrics, and geometrical prints.

Polo ($40), Cardigan ($50) and Shorts by Top Man. Bag ($298) by Marc by Marc Jacobs and Espadrille ($78) by Jeffrey Campbell.

With a robust heritage of producing high-end athletic and lifestyle fashions, PUMA has upped the ante on its creativity and joined forces with contemporary African artist Kehinde Wiley. Wiley is a unique talent, very well known for his portraits rendered against intricate backdrops of graphics and patterns. Coupled, Wiley and PUMA birthed an African spirited campaign that melds bright colors, rich graphics and portraits to produce a line of apparel, footwear, and accessories that are bleeding-edge, but still very PUMA. Ushering a historic event unlike any other, the World Cup 2010, which be held in South Africa is the genesis behind this initiative. Simply, the collection is an African art and fashion jamboree, juxtaposing classic portraiture with modern patterns and prints.

Highlights of the line include, the Limited Edition v1.10 Kehinde Wiley boot, where only 302 unique pairs will be released and two Kehinde Wiley T-shirts.

Limited Edition v1.10 Kehinde Wiley boot

Kehinde Tee

Kehinde Puzzle Tee

Pieced Track Jacket

Shopping for vintage can be a fun and thrilling activity.  It can also be very challenging and more frustrating than shopping in a retail store.  During a recent presentation at Paper Dress Vintage in London, I shared my top  ten tips for vintage shopping.  Before you begin your next vintage shopping outing, consider this strategy to help you execute the best trip possible:

1. Do your homework. - There are many types of vintage shops.  Some may specialize in denim, others in western or military wear, while others may focus exclusively on menswear or womenswear.  Just because you find “ABC Vintage Shop” online, doesn’t mean that the store carries what you want.  It’s important for you to give them a call before going, or do a little investigation online to find out exactly what goods they carry.
2. What are you looking for? - Vintage shopping can be a fun hobby or a serious passion.  In either case, it’s a good idea to know what you’re looking for before venturing out. Having an idea of what you’re in the market for will help to narrow the focus of the hunt.
3. What’s your budget? – With vintage, prices can range greatly, depending on the era, the rarity, and brand of the item.  Also, some vintage shops may be less expensive, catering to students and young hipsters, while others can be very expensive, catering to collectors and designer label seekers.  Begin with your budget in mind.
4. Know what suits you. – Just because it’s vintage and it’s hanging on a rack doesn’t mean it’s going to look good on you.  It’s important to consider your body type, the texture and bulk of the fabric, the silhouette that it creates on you, and the scale of the pattern.  Ignoring any of these considerations could result in a fashion fatality.
5. Know what trends are hot. – Be aware of what’s hot and what’s current.  For example, if animal print and faux fur are in this fall for women, then opt for a faux leopard stole as a way to incorporate this trend into your wardrobe.
6. Ask for help. - Don’t be afraid to ask the staff for help.  They usually really know their vintage eras and they’re normally very familiar with the store’s inventory.  So if you’re looking for a fringe dress from the roaring 20’s, a simple question can prevent you from spending precious time needlessly searching through racks of dresses.
7. Try it on and inspect it. – Finding the perfect item that actually fits can be thrilling.  However, don’t let the excitement distract you from focusing on the small details.  Be sure to inspect the seams, zippers, and look for holes and non-removable stains on the garment since it most likely cannot be returned after purchased.
8. Don’t be afraid to alter. - Just because the sleeves of a jacket are a little too long or the bust of a dress is a little too big, don’t rule it out completely.  Sometimes a minor alteration can transform a garment from good to spectacular.  While alteration fees can get pricey, the garment may be worth the extra cost of a nip and a tuck.
9. Consider Cost vs. Rotation - Not sure if you should spend $400 on a vintage dress?  Considering the Cost Per Wear may help you justify the purchase.  To calculate the “cost per wear” simply divide the cost of the dress by the number of times that you’ll wear the dress in a single year.  The principle is that the more wear you get out of an item the more cost-effective it is.
10. Mix it up. - I love vintage, but I never wear it head to toe.  Try mixing vintage with modern to inflect your own personality and style.

Happy shopping!